It is the conversation that no Raptors fan wants to have, and yet, over the next month the whispers will only intensify. Kyle Lowry is a free agent to be this upcoming summer, Toronto appears a couple notches below true contender status, and the future Hall-of-Famer is a clear and obvious difference maker for those eyeing the NBA’s biggest prize.

The trade deadline is 3:00 p.m. on March 25th and so teams that feel they’re a piece away might finally be ready make that big, bold splash. Toronto should be well aware of this. After taking a big swing for Kawhi Leonard and Danny Green in the 2018 off-season, they still felt they were a move away from maximizing their potential and gave up a bit of both present and future for the services of Grizzlies centre Marc Gasol.

Ironically, there are several parallels that can be drawn between the relationship Gasol shares with Memphis and the one Lowry does with Toronto with the major exception of course being that the latter already won a ring with the team he’s synonymous with. Lowry’s agent Mark Bartelstein of Priority Sports and Entertainment quickly shot down a report by the Philadelphia Inquirer’s Keith Pompey that mutual interest exists between the Sixers and the soon-to-be 35-year-old guard, a report that also suggested both the L.A. Clippers and Miami Heat are interested.

Even if this report is indeed unfounded, it is fair to ask what both Lowry and the Raptors want.

Lowry has shown no signs of slowing down yet, averaging 18 points, 5.5 rebounds, and 6.5 assists while shooting 39.5 percent from deep through 26 games this season. He may have missed out on his seventh All-Star appearance but has been an inspiring force behind the Raptors’ resurgence from a 2-8 start. With the roster taking a severe dent in terms of leadership and experience after the departures of Serge Ibaka, Marc Gasol, Kawhi Leonard, and Danny Green over the past couple seasons, Lowry’s leadership and toughness has been at the forefront. Other teams may have continued to slide further into the abyss, but he called out this group’s complete lack of swagger and inability to execute for long periods and challenged them to do better. Now fifth in the East with a 16-17 record, the Raptors are well positioned to claim a top-four seed and compete for an extended playoff run. They’re not here without him and any move—considering the options available—likely lowers the ceiling for this season.

Which situation is less optimal: [the Raptors] casting emotion aside as they did with DeMar DeRozan and Dwane Casey and having a less than amicable split or having a fifth key free agent depart (Leonard, Green, Ibaka, Gasol) with zero return over the course of three off-seasons?

The other side of the argument is that it is perhaps time to take the training wheels off to further accelerate the growth of Fred VanVleet, Pascal Siakam, and OG Anunoby. Lowry-led lineups in Toronto have long had a history of masking struggles elsewhere, but at nearly 35 he can only be counted on for so much longer. The Raptors are 6-1 this season in the absence of their veteran leader and while that’s by no means indicative that the team is better off without him, it does lend to the thinking that a post-Lowry era won’t be all doom and gloom. VanVleet has made significant strides as a playmaker and his decision making in the pick-and-roll has been Lowry-esque at times—the student is becoming the master. Siakam has made a leap with his ability to facilitate the offence while Anunoby and Norman Powell have grown more comfortable with greater offensive responsibility. The front office also added some insurance at the point guard position by drafting Malachi Flynn with their first round pick this past draft.

As far as considerations both President Masai Ujiri and GM Bobby Webster have to make, optics and asset management have to be key among them. Which situation is less optimal: casting emotion aside as they did with DeMar DeRozan and Dwane Casey and having a less than amicable split or having a fifth key free agent depart (Leonard, Green, Ibaka, Gasol) with zero return over the course of three off-seasons?

The residual effect of how much loyalty means in Toronto after the DeRozan trade may have faded in the afterglow of a championship, but what message would it send to the remainder of the core if the franchise operated in similar fashion with Lowry? Fool me once… Lowry has cemented his status as the greatest Raptor of all-time with both tenure and a championship. For that reason, the Philadelphia native’s blessings for a trade, whether it be the Sixers or any team, seem a must.

Another difference is the potential scenario in which Lowry leaves “for nothing.” Unlike the past two off-seasons, the Raptors would actually have cap space to benefit from and that’s something worth having. Giannis Antetokounmpo is no longer available but the likes of Victor Oladipo and Richaun Holmes—both under 30—are notable difference makers who can provide impact over a longer term. Toronto’s front office put in the hard yards to line up the books for the 2021 off-season, and it would likely take something out of the ordinary for them to pivot at this stage. 

Almost a year to the day Lowry played his most recent game in Toronto, what does appear closer to reality is the time to say thank you and good luck. There have been more of those goodbyes than Raptors fans would like over the last few years, but if there’s any lesson to take from the ones before, it’s that there’s not much value in worrying over what might be when there’s plenty to enjoy about what is.